Can Only Go Up From Here
by ObsessionsOTP
Summary: Emma and Henry Swan have the life they have always wanted; family and friends that care for them and a place they call home. Killian Jones is not as fortunate; no friends, no family, no home. How will their lives change when he meets a beautiful and stubborn woman and her equally stubborn yet spirited son?
1. Below My Feet

A/N: Hello again! I found time to write! Yay me! This has been something that has been plaguing me for sometime now, so I decided to go with it. Since this one contains musician!Killian it will contain songs, none of which are mine. I will only mention the song and artist as part of someone in the story saying the name and artist or through the name of the chapters, since I can't actually put the lyrics on this site. But they will be included on my Tumblr versions (deadmen-tell-notales), if you wanted to read it with the lyrics.

That being said I do not own any of these characters! That belongs to Adam and Eddy and ABC.

I don't know how long this will be so... yeah, let me know what you think. As always criticism is always welcomed. I would like to develop as a writer.

* * *

Holding tightly to the helm of the ship, he barked orders to his crew. The storm gave the pirates an unexpected turn of events; they were sailing smoothly across the oceans, exhausted from their most recent adventure but buzzing with excitement about their hefty haul, treasure that would accommodate each sailor for months to come—assuming they could survive the damned storm, of course.

"Captain, we can't hold on much longer!" a crewman yelled over the sound of the waves pounding against the side of the ship.

"You must, and you _will_! That's an order!" the captain roared over the deafening wind, expertly steering the _Jolly Roger_ away from the storm. "Any who dare show any cowardice will walk the bloody plank when we escape this storm." He glared at his crewmen, "And we _will_ out run this bloody storm."

At their captain's threat and confidence, the crew held on tighter and went about their tasks with more will. The captain maneuvered the ship with great skill and speeds, leading the men out of the storm's reach. The pirates let go of the railings and ropes they used to anchor themselves with and took a moment to collect their bearings. Mr. Smee, the ship's quartermaster, lifted his fist in the air and yelled, "To our captain!"

The other men joined in as they raised their own fists in the air, "To Captain Hook!"

The captain watched the men all preparing their second round of shouting. Instead of their boisterous cheer, a shrill ringing tore from their lips.

* * *

Henry's head snapped up from his desk, the blatant ringing signaling the end of his last class of the day. He watched the rest of the students file out of the classroom in a sleepy haze before realizing where he was.

"Planning on staying here, Henry? I'm sure Leroy would appreciate the help," Mrs. Blanchard—now Nolan—his biology teacher (and aunt) mused while he hurriedly stuffed his binder in his backpack.

"Uh, no," he replied with an embarrassed chuckle. "Sorry for falling asleep in class. Won't happen again, promise," he continued as he stood and swung his backpack over his shoulder.

"I'll hold you to that promise. Maybe you should stop playing your video games and go to sleep at a decent time," she scowled playfully.

The truth was that he and his mother stayed up late eating ice cream and watching movies. It was their thing, watching Disney movies until one of them fell asleep. He'd fallen asleep watching Peter Pan, which explained his dream. He'd never admit that to his teacher/aunt though. "I don't know what you're talking about," he replied instead.

"Uh-huh," she shook her head with an amused smile. "Remind Emma about dinner tomorrow, will you?"

"Sure thing. See you later, Mary Margret."

"It's Mrs. Nolan at school!" she yelled behind him as he made his way through the mostly empty school hallway.

Henry only laughed softly to himself. He's known Mary Margret—or rather, Mrs. Nolan since he was still in the school building—most of his life. She was married to his uncle, David Nolan. David didn't find Emma or Henry until Henry was eight years old, having been looking for his long lost sister for years. After his mother finally felt comfortable enough around her brother—and only after she verified they were actually related—things had gotten incredibly lighter. It wasn't just him and his mom anymore. They had people who cared about them and loved them unconditionally, and his mother was all too happy to open that possibility to Henry. Ever since then, they'd been an unbreakable family, growing with the friendships they'd made along the way—friendships that grew to the point that they were just as part of the family as David and Mary Margret. Although he was young at the time, Henry still remembered how his mother struggled to provide for him and make sure he'd never feel alone, but now he had more family than he knew what to do with.

A sudden honk from a car broke Henry from his thoughts. He looked up to see his mother's car parked right in front of the school with his mother waving him over, trying to catch his attention.

"Hey, kid, need a ride, or are you just going to float on those clouds of yours?" she asked him as he slid inside the car; she obviously noticed his wandering thoughts.

"I think riding with you would be far safer," he laughed. "Wouldn't want to run into a tree or anything."

Emma shook her head with a smile as she put the car in gear and drove away from the school. "At least this time you weren't consumed by your phone."

"Says the mom who is _always_ consumed by _her_ phone," he fired back with mock annoyance.

"I don't know what you're talking about," she smirked. "How was school?"

"It was alright. Got an A on my Algebra test and I finally figured out what to write about for Uncle Booth's class," Henry sighed resting his head on the back of his seat, as if the mere brainstorm for his English assignment seemed exhausting. "He's you best friend mom, couldn't you just tell him to make this easier, for everyone?"

Emma laughed at her sons complaining. "He does it on purpose. Wants you guys to find your authorial voice or something. He's especially hard on you because he thinks you got a talent for writing. And I agree with him, you're great at writing," she said proudly.

"I don't mind the writing, it's the coming up with something in the first place that gets me."

"Well, you said you figured it out, so what's it going to be?" she asked intrigued.

"Pirates."

Emma looked over at Henry, a knowing smirk playing at her lips. "Peter Pan?"

"Something like that," he said sheepishly. "But like I said coming up with where to start is the hard part."

"Well, how about you take a break from your meticulous brain storming and we go grab some pizza. We could eat by the docks?"

Henry looked over his mother and smiled excitedly, "Our spot?"

"Duh. Where else?"

* * *

"Two dollars? That's it? Look I know my stuff is cheap but not that cheap. Take those somewhere else, a shelter perhaps," the man sneered, shooing Killian away as if he were merely a dog.

"Look mate, I'm not one to beg and I haven't eaten since yesterday, this is all I have. I am willing to work for it. I'll clean dishes if you'd just—"

"Work here? You'll scare away my customers. I said no, I ain't feeding no street rat. Now get the hell out of my restaurant!"

There was a ding from the door, announcing someone's arrival behind him. Killian grabbed his two single dollars from the counter and stuffed it in his pocket.

"Right then, have a good evening," he mumbled as he turned to leave.

"Street rat," he heard the man breath in annoyance behind him. Killian grabbed the guitar case and the duffle bag by his feet, not looking up as he walked by the customers that had arrived. Instead, he rushed out of the restaurant, his stomach growling harder as he went.

He made his way down the street, turning into the darkened alleyway he called home. The one way alleyway seemed like the more practical option when he arrived more than a month ago. It provided him with protection all around him, only having to worry about what was going on directly in front of him.

He sat on the hard damp concrete, thinking what his next move should be. He had to keep moving. He'd hoped to find a new beginning in the town of Storybrooke, but after weeks of trying it was clear he had overstayed his welcome. Most of the shop owners knew he was homeless and denied him any chance at employment. He'd taken to play his guitar to earn some money, but even that had dwindled down in the weeks he'd resided in the small town. He'd only earned two dollars from an elderly couple that day, no one else paid him any mind.

How could he be so delusional in thinking that this time would be different? Every town, every city, and every state he traveled to only brought him the same fortune—or rather lack thereof. He'd learned that people thought of him as a villain of sorts, believing that he committed terrible mistakes and crimes that lead him to the life he has. It seemed easier to think the worst of someone than believe them a good person. Not that he'd say he was a good person.

Getting up from his spot on the floor, he stowed away his duffle bag in a concealed spot high off the ground away from curious eyes and grabbed his beaten guitar case. He walked the three blocks to the docks, a place he had frequented throughout his stay, his grip on the case tightening with every step. Ever since he was young, he found a certain comfort in the ocean; the sound of the waves crashing with the shore and the salty air of the sea never failed to calm him or help him work through his emotions.

Killian walked towards what had become his usual spot by the boats but stopped short when he saw it was already occupied. He turned quickly, not wanting to interrupt their own time of relaxation, choosing to sit on a ledge that overlooked a sandbar instead. The view was just as breathtaking and just what he needed. He breathed in deeply feeling his muscles instantly unwind. He went on to open the guitar case, holding it open for a moment as he collected his thoughts. He set the notebook that laid on top to the side and took out his guitar. He took another breath as he adjusted the instrument high on his chest as he molded to it. It was the only thing that he still owned of his old life, a life where he had a roof over his head and at least two meals every day but the same emptiness he felt every day. The guitar used to be his brother's, a gift from their mother when he turned fourteen. It became his prized possession when Liam died, the only thing that kept him from losing himself completely sometimes.

He began to strum the strings with practiced skill forcing his memories away as he tightened his grip. Images of his brother, lifeless and bloodied, assaulted Killian's thoughts as he sang softly, the song digging up old memories he wanted to keep buried. His voice became thick with emotion as he allowed himself to grieve for just a single moment. His fingers danced along the strings as he played a soft melody that increased in intensity as he kept singing, his tone becoming almost angry and sarcastic as he shook away the self-pity. Each strum on his guitar became more insistent as he sang louder, letting his emotions run through him unchecked as he submerged himself completely into the song.

He counted to ten after he strummed the last notes of the song, breathing in twice before opening his eyes, not knowing when they had shut closed. He missed his brother terribly which was why he knew he had to fight harder, look further. He needed to put his life back on track before he lost himself irrevocably. He would not go any further, he would stay in Storybrooke and begin his life. He survived for himself, now he needed to find something to live for.


	2. Chapter 2

I know it's been more than a month but you know how life can get. One minute you have two days off the next you're going none stop with work and school for a month. Well this chapter doesn't contain any songs but the next one will. As always reviews are always greatly appreciated.

* * *

"I don't know, kid. A pirate who rescues a princess? Aren't pirates supposed to be the villains?" Emma asked between bites of her cheese pizza. They had been sitting on their bench at the docks for almost half an hour; Henry regaling her with his plans for the English assignment.

"Well yeah, but that doesn't mean they have to be villains forever. People can change," Henry explained. Emma looked at him with an ' _I'm not so sure'_ earning her an amused shake of his head. Emma knew better than to believe in fairy tales, the only people who changed completely were in movies and books, it's why people liked to lose themselves in them so much. They're not realistic.

"You _are_ writing fiction," she said with a small roll of her eyes.

"Exactly. _I'm_ writing it," he said as Emma stuck her tongue out playfully. "And in my story the villain gets to prove himself to the princess," he continued, a hint of pride in his voice as he thought about his story.

Emma was about to ask how he planned to do that when she heard a guitar playing a few yards away from them. She looked over Henry's shoulder and saw the man from earlier in the pizzeria. His hair was askew, his clothes wrinkled and torn in various places, an open guitar case next to him as his singing became louder, almost desperate. Henry stopped mumbling about his story beside her and turned to follow her gaze, watching the man play in a sort of awe.

"Below my feet," Henry said then.

"What?" she replied, though it came out almost a whisper as she was too entranced on the singing stranger.

" _Below My Feet_. Mumford  & Sons, remember?"

Emma shook herself out of her trance and listened to the lyrics more intently, recognizing the words Henry and her have sung to many times before. She had to admit the guy was pretty talented, playing the guitar with ease as he sang the tune effortlessly.

"Hey, isn't he the guy from the pizza place? He was trying to get food but didn't have enough money, maybe we should offer him some of ours?" Henry asked looking at her with hopes that she'd agree. Times like these she thought that if she had done one thing right it was her son. He was such a kind hearted kid and she was proud of that. She couldn't deny him his request, he just wanted to help the guy out after all. David and Mary Margret had engraved it in his head to help others whenever possible, something she herself tried to work on thanks to her brother. Her brother; _that_ still felt surreal at times.

"Yeah, you're right. I'd say he's earned it for providing us with good music, right?" she rationalized. Truthfully she just wanted to see him clearly, for safety purposes only of course. She _was_ the Sheriff after all and she'd never seen this guy before, it was her job.

They stood up from the bench while Henry collected the box of pizza, they walked the short distance and stood behind him. He was taking deep breaths—was he counting?—his eyes closed. Henry cleared his throat to get the man's attention, his body language portraying his nervousness. The man looked over his shoulder, defeat written clearly on his face. His eyes fell on Emma first, his features morphing into an almost awestricken expression. Emma felt her cheeks redden, even with his hair sticking out every direction and the slight filth that seemed to cover him he was still, by far, the most gorgeous man she has ever seen. His eyes an impossible cornflower blue that she couldn't look away from. She tried to think of anything to say that would break the eye contact but she couldn't form a decent thought in her head.

"We heard you sing," Henry said beside her, effectively breaking their eye contact as the man turned to her son. _Dammit Swan, get a hold of yourself,_ she berated herself. "You're good," Henry went on. The man gave Henry a sheepish smile while he scratched behind his ear.

"Thank you, lad," he responded in a lilting voice.

 _Fuck me,_ Emma thought, of course he had an accent, an Irish one at that.

"We were wondering if you wanted a slice of pizza, as payment for playing so well?" Henry added nervously, not wanting to offend the guy by calling him out on his situation.

The man chuckled sadly shaking his head slightly. "If you are to be so kind lad the least I can do is give you my name," he said extending a hand for Henry to shake. "Killian Jones, at your service."

Henry smiled and shook Killian's hand while holding the pizza box in the other. All of his nervousness seemed to have slipped away, an ease overcoming his body, making it seem like he was a hundred percent comfortable with the guy. Killian smiled softly at her son and her insides melted involuntarily.

"My name's Henry. This is my mom, Emma Swan," he introduced. Killian's eyes fell on hers again and, _shit,_ why did this have to happen to her.

"Pleasure," he said extending his hand again. Emma shook it, giving him a tight smile, blaming static electricity for the tingling she felt at his touch.

"Likewise," she mumbled. He gave her a knowing smirk, an eyebrow cocked in amusement.

Great. Even though he was homeless he knew damn well the effects his looks had on her. Cocky bastard.

"How about I play you a proper song lad, only then have I truly earned what you offer," he suggested as he slowly looked away from Emma. "Which song would you request of me?"

"We actually don't have much time for another song," Emma interrupted just when the kid was about to respond with too much enthusiasm; she really didn't need to add another tally to this guy's yes column. "Someone has to go to sleep early so he doesn't fall asleep in class," she said, hoping to steer the conversation to an end and go home, away from the guy whose eyes she hopes she doesn't dream about.

Henry grunted in annoyance. "I apologized. Besides I already knew everything in that chapter, Mary Margret was just reviewing it. That's why I fell asleep in the first place. I was bored—don't tell her I said that."

"You are going to sleep early tonight, kid. End of discussion," Emma ordered sternly.

"Fine."

"Good."

She heard Killian chuckle softly, causing her to shiver. She tugged her leather jacket closer to her as if a cold wind had caused the sudden chill. What the hell was wrong with her? He was a stranger for god sakes. A very attractive stranger but still a stranger nonetheless.

"We should get going, kid."

"We can't just leave him here," he stated matter-of-factly.

"Henry," Emma gave him her ' _Really?'_ face. What did he want her to do, take a complete stranger home? (Of course she'd done it before, when she needed a certain itch scratched, but she wasn't about to tell her son that. Ever.) She wouldn't let a stranger, no matter how attractive, into their home.

"Lad, really that's not necessary. I have my own home to go to."

 _Lie._

"No, you don't," Emma bluntly stated. Killian's eyebrows shot up in surprise. "Have you tried Granny's B&B? I'm sure she'd let you stay for a day or two. Maybe even offer you a job?"

"Ah, how could I forget to ask for a room in the only bed and breakfast in town?" he deadpanned. "Of course I've tried, darling. Let's just say I overstayed my visit. As for employment, she didn't have enough in her budget to hire another person. And I have been kicked out of most other places in this quaint town. Here I thought small towns were supposed to have the nice folks," he smirked sarcastically.

 _And_ the shoe drops. Emma rolled her eyes at his defensive remarks. She knew the nice guy act wouldn't last very long. She was about to respond with her own smart ass comment but stopped short when she looked in his eyes again. She saw the annoyance and the bravado but she also saw a faint glimmer of sadness, one she had seen in the mirror more times than she could count. She had to help him, it was the right thing to do. Paying it forward and what not. She sighed heavily.

"Look I may know of a place that's hiring, if you're interested?" she offered.

"That… would be much appreciated," Killian sighed in defeat.

"And maybe we'll throw in new clothes and a haircut too," Henry added.

"It _would_ help if you didn't look so… homeless," she interjected before Killian could say no, unable to find another word that wouldn't sound so offensive. Killian just laughed at her less than subtle ways.

"Quite the persistent duo, eh, Swan?" he remarked, an eyebrow up in amusement.

"He is my son and I am his mother," she replied. She couldn't help the burst of pride at the thought of her and Henry being so alike. Sometimes all she saw was Neal's care-free personality in him, which wasn't entirely a bad thing.

"We'll point you in the right direction," Henry said extending his hand for Killian to shake, a wide smile spreading on her son's face. This time it was with a new found respect for the wayward man, a promise that he'd help him in anything he could and she was fully on board with that. It was Henry's way of telling him that he understood Killian's need to do this on his own and how much it took him to accept their offer, small as it was. It would have been nice to have someone to guide her the way Henry seemed so eager to guide Killian when she was in the same situation, or even when she was still in the foster care system. By the time David had found them she had already gone through her fair share of struggles and heartbreak and she had found a way to survive with her son on her own. She was going to help Henry help Killian. And it had nothing to do with the way the man was smiling brightly at them.

"Then it could only go up from here, lad," he grinned at them.

Nothing to do with that at all.

* * *

Killian didn't know why Henry was so eager to help him or why Emma let him or even supported him. He had been alone for so long, he'd started to believe he wasn't worth anyone's time or effort. He'd taken to fighting by himself, used to doing everything himself. There were a few times when he succeeded in finding a job, succeeded in starting a new life, only to muck it up with his temper and letting his demons run free while he drank himself into oblivion. He spent more time behind bars at any police station for picking fights than in an actual room with an actual bed. He wasn't able to move past the sorrow and the rage that was his past, always getting carried away with the shit storm that was his life. It only took a snarky comment from a stranger to make him see red.

It wasn't until two months ago that he decided to really make an effort to change his life. At the time he had been on a random dock in New Hampshire drinking and playing his guitar aimlessly on a boat he snuck into for shelter when his brother's journals caught his eye. He'd very often seen his brother writing in various notebooks, but he'd never asked what it was he wrote down so meticulously, never having the will to peer inside once his brother passed. The pain he felt at even _seeing_ the damned things caused him to double over with grief. It took him nearly five years to open them, to finally muster the courage to open the journals that resided in the guitar case, seeking desperately for any comfort that only his brother could provide.

He had endured four days without a decent meal and had been kicked out of the square he was performing in by security. He grew more and more tired as the weeks passed, with no end to his suffering in sight. He contemplated giving up entirely as he opened the bottle of rum he managed to swipe from a poorly secured liquor store. He stopped his slow strumming of the guitar and stared at the worn out notebooks for what felt like forever; the vivid image of his brother writing in a corner, brows furrowed in concentration, finally pushing him to pick up the notebook. He opened the first journal to the first page, Liam's formal penmanship adorning the paper with random entries. His face instantly scrunched in an attempt to stop the tears; he read every single word in all three notebooks; every lyric, poem, and personal musings that had inspired some kind of emotion in his older brother enough to want to write it down.

It had been a long time since he had felt that close to his brother. He vowed then that the next town he fell in was to be the town he would find a home in, and he wouldn't stop until he had succeeded. _A man unwilling to fight for what he wants, deserves what he gets,_ it was Liam's dictum, and was ever present in every lecture he gave Killian. The sentence was written arbitrarily throughout several pages as well. It was last written two days prior to his murder.

Killian wept all throughout that night.

He awoke when two policemen shook him abruptly out of sleep and escorted him to the police station for trespassing. After he was released a day later he'd worked to earn enough money for a bus ticket, getting one that took him the farthest for his money. He was dropped off in Storybrooke, Maine. After two months of searching for a job and a place to stay (and effectively failing) his resolve started to slip, that is until Henry and Emma came along. He didn't like the idea of needing help, wanting to get ahead by his own will, but for some unknown reason he couldn't deny either of them anything. Henry was such a kind and spirited lad; he moved Killian with his vigor and enthusiasm to help him, a complete stranger. And Emma—he wasn't absolutely sure about her if he was being honest with himself. He recognized that she must have gone through her own struggles, recognized the haunted look in her eyes, the look one gets when they have lost too much, gone through too much. He knew the moment she seemed to see the same in him causing her features to soften a bit in understanding. What vexed him the most about her was that she was the one who explicitly offered him their help, Henry had only really asked for permission. She could have easily denied Henry's request and gone home and yet she must have seen something in Killian, enough to give him a chance. Why would she give him a chance at all, especially after being a bit reluctant? What could she have possibly seen in him that was worth her effort?

He accepted their help somewhat defeated, something told him Henry wouldn't have taken no for an answer if he continued to argue anyway.

"Quite the persistent duo, eh, Swan?" he'd said.

She smiled then, obvious pride rolling of her, looking to her son and back at him and he'd never seen anything quite so breathtaking. Not even the sea in the morning light could compete. Henry extended his hand in what was more of a promise. He could feel the boy's determination in his firm grip. Killian squeezed his hand in kind (it was all he could do to not let his emotions overwhelm him). As they said their goodbyes and arranged to meet after the lad was out of school, Killian could see the wall Emma began to build, as if she'd just realized she'd let her guard down around him. He was surprised at how quickly she hid behind the mask and with such ease, a lesser man would not have noticed; he did though and so he would respect her wishes and keep his distance for some time, even though he wanted to know more and more about both Henry and Emma—especially Emma— and their lives with each passing second, but he had to straighten himself out first. He wouldn't let them down, he would make sure to make something of himself now more than ever, and he would prove to them that he was worth their efforts.

* * *

The next day Killian sat on his now unoccupied bench, watching the waves lightly crash into the boats in the marina. He counted the waves quietly, not allowing the hope that had sparked to life the night before to get out of hand. He knew better than to give in to hope so completely, knew the disappointment that came after could be crippling. As the afternoon stretched into the evening, the sun setting in different shades of orange as night began to fall, it became crushingly clear that his efforts of expecting the worst so as to not get hurt failed completely. Killian stood grabbing his guitar case from its spot on the floor, clutching the handle in efforts to keep the disappointment away, to keep a straight face. He'd hoped that they'd showed but he knew the chances of that actually happening were slim to none from the beginning. How could he be so foolish in believing himself worthy of their attention and generosity? They probably did mean to help him but thought better of it in the morning; he was a stranger after all, they didn't owe him anything.

Killian walked along the shops, head down as he walked to his hole in the wall he called home, until he ran straight into a firm body.

"Oi! Watch where ya going, will ya!?"

He should have let it go, should have apologized and kept going, but the disappointment and regret he felt quickly turned into a burning desire to bash the guys face in.

"I could say the same to you, _mate_ ," Killian spat back stepping into the leather clad man's space. The man was about to respond when he looked down at Killian's guitar.

"You play?" he asked with cautious curiosity.

"And what's it to you?" Killian replied annoyed at the guy's change in attitude.

"Bloody hell," he sighed. "I know I was just about to smash your face in—"

"Ha!"

"— _but_ luckily for you I'm in need of a guitarist."

Killian stared at the man as if he had three heads. He was about to get into it with this guy in hopes of relieving some anger and here he was offering him a job?

"An answer would be nice, mate, before the sun comes up again," he said sarcastically.

"Uh… aye. Yes I-I accept the offer," he responded still dumbfounded.

"Fantastic. Name's Will Scarlet. Your new boss," he added smugly.


	3. All I Really Want

Emma sat in the interrogation room for hours going from kid to frustratingly, tight lipped kid trying to squeeze out information on their little band of misfits. She and David caught four of them after getting a call from Mr. Clark about some teens stealing from his pharmacy; it was a lengthy chase that she will surely feel in the morning. She watched as David asked question after question, make empty threats, and nearly jumping out of his chair when he was only met by silence. These teens were tough and they had a look in their eyes that was eerily familiar.

She tapped David on the shoulder indicating it was her turn. She was usually their big gun, using her experience as a bails bonds person and her super power to break the stubborn suspects. David shook his head at the teenager seating across from them, mumbling about how he tried to save him the trouble and left the room. Emma watched the boy for a moment, noticing his stone face expression as well as the sweat blooming on his temple. Emma smirked slightly before sitting and leaning in, speaking in a soft tone, "I'm going to let you in on a little secret: I'm pretty good at knowing when someone is lying to me."

She held in her smug smile as the boy gulped nervously before schooling his expression again. "Okay, let's start with your name."

After a pregnant pause he murmured, "D-Darien. M-my name's Darien." He gave a defeated sigh, shoulder's slumping down and in that moment Emma saw a scared kid not a would-be-criminal. Emma leaned back and whispered softly, trying not to scare him further.

"I can get you back home but you have to help me find the person in charge." She stared back at Darien as he watched her, gauging whether or not to trust her. She gave him a small reassuring smile that was immediately given a response.

"His name is Peter but sometimes we call him Pan because he calls us the Lost Boys like in the movie _Peter Pan_. He thinks he's helping us but most of us just want to go back home. I want to go home," he whispered nervously, as if Peter was somehow there listening. His eyes welled up with tears and Emma's heart broke for the kid. She'd find this Peter guy and any other "Lost Boys" and put them back where they belonged, with their families.

"I'll make sure you get home. I promise," she gave him a soft smile as David came back inside. "You're going to tell David everything you know about Peter and your family and we'll get you home. Okay?" He gave her a small nod as David ushered him to his office. After Darien talked to the other boys they all started giving all the information they had; a couple hours later David and Emma were able to find their respective homes.

"I was with him for more than an hour and he didn't so much as utter a word. I'm still trying to figure out how you make them talk after a few minutes," David told her as they walk to his police cruiser.

"In this case they were just kids. And I was able to appeal to what every kid needs," she explained with a shrug. "A mother."

"Well, job well done Sheriff Swan. These guys get to go home thanks to you," he replied with a proud smile.

She started to respond when she spotted Henry walking towards them in what was clearly not his usual cheerful mood. David patted her on the shoulder volunteering to escort the boys' home. When Henry stopped in front of her as David drove past them Emma was surprised to see that her son was visibly angry.

"Whoa, kid, what's with the face? What's wrong?" she asked concerned. Henry wasn't the type of person to get angry at anything, his carefree personality usually dodging that emotion.

"What's wrong? Mom I've been waiting for you at home to meet up with Killian for hours. We were supposed to help him, remember?"

Emma pinched the bridge of her nose as she tilted her head upwards with a grunt. _Fuck_.

"I completely forgot, kid, I'm sorry. Work had a lot more activity than usual. Maybe if we go to the docks now—"

"He's not there," he interrupted her with his own frustration. "I checked before I came over here. I figured something came up but I thought you would have at least given me a heads up before we stood him up."

Emma's face fell at Henry's disappointment, hell her whole mood went to hell knowing she had let him down. "I know, you're right. I should have called but it completely went over my head, Henry. But we don't owe him anything. We gave him some food yesterday and he didn't go to sleep hungry because of your generosity. I'd say he'd be grateful enough for that. Maybe he didn't even show up and you're thinking that we stood him up."

Henry shook his head at her attempts to reassure him. "I asked Mr. Webber down at the docks if he saw anyone waiting by the benches and he said that there was a man carrying a guitar case sitting at our bench for most of the day. He did show up and he waited for us. I know we didn't owe him anything but now we do. I made a promise and I intend to keep it."

"Mr. Webber?" Emma stared back at Henry shocked by his utter determination to help this complete stranger. And how the hell did he end up speaking with the old recluse that lived by the docks? He never spoke to anyone and looked every bit a retired Gandalf that put on some weight from inactivity. She intended to ask just why of all people he spoke to Old Man Webber when Henry turned abruptly and walked away. "Where are you going?"

"I'm going to see if I can find him before it gets too late," he responded over his shoulder. "Like I said I made a promise."

Emma struggled pulling her jaw off the ground as she watched him walk further away. She was dumbfounded by his outburst, he'd never spoken to anyone like that, much less her. She wondered what this was really about because as much as she knew Henry wanted to help this guy out she knew her son well enough to know this ran deeper. It was clear to her that Henry was growing-up, perhaps a little too fast for her liking, and that change will surely alter their relationship. He wasn't a child anymore and much to her dismay it was time to stop treating him like one, at least when it came to these situations because if there was one person she needed to be on the same page with it would be Henry.

She shook herself from her stupor jogging to catch up to him, full intention on finding out just what was truly troubling her son. She grabbed the inside of his elbow gently to force him to stop and look at her.

"Why is this so important?"

He casted his eyes to the sidewalk as he took a deep breath before looking back up at her.

"I just want to help him out. Nothing more," he replied, his face carefully masked (or so he thought).

Emma snorted at his response. "Seriously, I'm your mom and I still have my superpower. Try again." They started at each other for a long moment, Emma silently pleading him to open up while he tried to come up with a plausible excuse. Thinking better of it Henry sighed and gave in.

"I don't want to be like my dad," he whispered.

Emma froze at his confession because what the _hell_ did Neal Cassidy have to do with this?

"What?"

Henry looked up to the sky and breathed in deeply again before explaining everything that had slowly built up inside. "He broke his promise to you. He broke his promise and because of that you went to jail, I was born in jail, and we had to be separated for a while because of it. He left us alone. And I know he doesn't know about me but he still left you and because of him everything was that much harder. He broke a promise and it ruined everything. I don't want to be someone who breaks promises and ends up ruining everything. I want to be able to keep my promises or at least try to keep them as best I can like you have shown me to do. And I feel like if I don't help Killian and I don't go through with it I'll ruin everything. Just like dad did."

Emma swore her heart broke into a million pieces in that moment. Henry had been carrying this weight for who knew how long and she was at a total loss as to how to comfort him. She cupped his face in her hands making sure he was looking her in the eyes as she tried to speak the words he needed to hear the most. His brown eyes shined with unshed tears but there was a determined gleam in there as well. She recognized the look, it was much like her own when she went on a "stubborn streak" as David called it. She definitely had to choose her words carefully and hopefully make him understand.

"I know what your father did was far from being honorable but he was a good person. You have to know that. He was scared, of what I'm not entirely sure of and I'm not saying I have forgiven him because I haven't; but he was a good person. And yes, he _doesn't_ know about you but I have a feeling that if he had he would have at the very least tried his best for you. He'd be here. Maybe I was being selfish by not telling him; but at the time I was too hurt to believe he would do right by us. He wasn't a bad guy but trust me when I say you did not inherit your father's inability to keep a promise. You got all his good traits."

She smiled softly at him as she thumbed away a stray tear from his cheek. Leaning in she kissed his forehead while squeezing him in a tight hug. She felt him relax into the hug seemingly letting go of the thoughts that plagued him, if only for the moment.

"Are you going to help me find Killian now?" Henry asked as he pulled away casually looking around to make sure no one saw their exchange. God forbid someone saw their shared moment, Emma thought amused, unable to hold back a roll of her eyes at her teenage son. She sighed heavily in defeat, of course he wasn't going to let that go.

"Why are you so stubborn?"

" _That_ I got from my mom," he replied with a sly smile dodging Emma's hand aimed at his head.

What was she going to do with this kid?

* * *

"Right now?"

Will Scarlet rolled his eyes annoyed by Killian's inquiries, "Yes now, I have to open the bar in an hour." They stood in the middle of the stage at the Rabbit Hole, Killian gripping the handle to his guitar case his nerves getting the better of him suddenly. Will sighed, walked across the room dragging a stool from the bar behind him and onto the stage, putting his hands on Killian's shoulders as he forced him to sit. He then firmly placed a mike stand in front of Killian and gave one command: "Sing."

"Are you giving potential band mates a hard time again, William?" said a tall, brown-haired man behind him mockingly. "This is exactly the reason we still have an open spot."

"Odd, I thought that was due to you stubbornly looking for the 'right person' for the band?" Will retorted as he twirled around, eyebrows high in challenge.

Killian watched as they began to bicker, accusing the other of random acts. He unclasped the case and went about preparing himself for a performance, nerves completely forgotten; his hand moved with practiced skill as he tuned the guitar.

"Don't worry you'll do fine."

Killian turned to see an attractive brunette behind him; she wore black leather pants and a black hat but the rest of her wardrobe was a brilliant red, red heels, red blouse, even her nails were a blood red. "I've heard you play around town. I'm sure they'll love you even if they won't openly admit it."

Killian stiffened. Of course she knew he was homeless but for some reason he didn't want anyone to know, at least not before he secured the gig. He thought he could get away with them not knowing for a bit since he knew for a fact he'd never seen Robin nor Will before, even in this small town. She seemed to understand immediately, squeezing his shoulder lightly. "I won't tell if you don't," she told him with a reassuring smile.

"I'd appreciate it, lass," he replied. "I'm Killian."

"Ruby," she shook his offered hand before continuing. "You know you won't fool anyone with that get up though, right?"

"So I've heard," he mumbled. "But I don't intend on keeping it a secret for long. Just long enough for them to see my worth, I suppose."

"I doubt they'll ask anything about where you live. It's not lying if they don't ever ask. But maybe I'll be able to help you out. Clothes and fashion are my expertise," she told him with a wolfish grin as she waved a hand above her outfit as if her statement was obvious.

Killian chuckled at her lighthearted attitude and nodded in agreement. "Many thanks, milady."

"Milady? Oh yeah Robin is going to love you for sure," she laughed as she walked off the stage to break up the still quarrelling men. "Are you going to let the man play or should we call David to separate you two again?"

Will and the man he supposed was Robin glared at each other before giving Ruby a single nod and finally turned their attention back to Killian.

"Apologies, mate. Go on," Robing gestured for him to begin.

Killian breathed in twice before he started playing the first song that popped into his head.

As Killian strummed out the last notes and looked over to the small group in front of him. Ruby smiled at him and gave him a quick thumbs up, Robin seemed satisfied and, dare he say, a little impressed, while Scarlet stood there with feigned indifference but Killian could tell he approved of the performance as well.

"So do I make the cut?" Killian asked after a moment, a smug smile pulling at his lips at their reaction.

"With an Alanis Morissette song?" Will scoffed.

"Hey! _All I Really Want_ happens to be a great song," Ruby defended.

"And it was a great rendition of the song. Welcome to the band, mate," Robin grinned extending his hand for Killian to shake and completely ignoring Will's scowl. Killian shook his hand firmly with his own genuine smile.

"Like we had a choice," Will muttered not so subtly.

Ruby lightly smacked him upside the head in mock admonishment. "Don't act like you don't like what you heard. That would just make you look like a bigger ass than you already are. Besides you're the one that brought him in."

"He's alright. And I only brought him because we were running out of time. It was pure desperation."

Ruby rolled her eyes as she walked to Killian's side and patted him on the shoulder as he packed away his guitar. "I think you'll fit in with us just fine."

"Not in does rags he won't. What were you doing swimming in the bins outside?" Will asked still trying to play off how impressed he was by Killian.

"Laundry day," Killian responded with a tight smile.

"So when will we start rehearsing? Tomorrow?" Ruby asked quickly with a quick, reassuring squeeze of his shoulder.

"Absolutely. As William said, we don't have much time before our next performance," Robin called behind him as he walked towards the bar to collect his jacket from a stool. "We'll meet here again tomorrow around four so we can practice while the pub is closed?" he asked turning to Will.

"Sounds good to me. Is it okay with the lady?" he asked looking over his shoulder to Ruby and Killian.

Ruby rolled her eyes, "It is fine by me, ass wipe."

"Wasn't referring to you, darling," Will grinned.

"Why aren't you a charming, lad," Killian responded, an arched eyebrow and a smug smile plastered on his face. "Worry not, I will be here."

Robin chuckled as he shook patted Killian's back in farewell. "Right then, see you tomorrow."

"Aye, see you then."

"Well," Ruby pipped up with barely contained laughter. "I'm leaving too. Killian walk me home."

At her request Killian sobered and nodded, "Uh, aye. Sure."

"Be careful, mate, she tends to bite," Will teased behind them.

"You're just bitter I haven't bitten you yet," she threw back in the same beat.

"Yet!" they heard him yell back.

Killian watched as Ruby laughed at Will's antics. She turned a slight shade of red, it was subtle but it was still there.  
"So, you and Scarlet," Killian smiled knowingly.

"What—no. There is no me and Will," she replied quickly, flushing a deeper shade of red.

"Why are you turning red then lass?"

"I'm not," she grumbled.

Killian hummed at her response, "Your secret is safe with me, Red."

He let out a hearty laugh when she pushed him with both hands.

* * *

An hour later Killian and Ruby came back to the bar and found a seat towards the back of the bar. Killian wore some clothes that were left behind by Ruby's ex-boyfriend, they were a bit tight but not uncomfortable so he kept them on. Black jeans and a buttoned down red and black flannel long-sleeved shirt which he rolled up to his elbows. He took a proper shower and felt better than he had in months.

He didn't know how everything seemed to turn on its head for him but ever since speaking with Henry and Emma the day before his luck just seemed to change. He understood that they didn't need to show up and though he was hoping for it he never expected them to show up, but the fact that they had offered him anything to begin with just made him want to get up in the morning and _do_ something. He just hoped if he kept on this path he'd finally escape the darkness that had been in him for so long.

Scarlet showed up by their table and chatted with them for a few minutes before suggesting Killian make his debut and sing some songs. He told Killian it was the perfect chance to do so since business was slow that night and there weren't too many people that would boo him. After lightly slapping Scarlet's arm Ruby grinned and encouraged him to go up to the stage, though he wasn't sure if she was for Killian's benefit or the fact that she'd be alone with Will.

As was his life however an already piss drunk patron got in his way a few feet away from the stage.

"I know you. You're that street rat from yesterday. You don't look it right now though. Were you trying to pull a fast one on me! Trying to get free meals and steal from me!" he slurred, shoving Killian on the shoulder. Killian shrugged it off trying to walk past the drunk man and avoid a scene. "You worthless piece of—"

Avoidance was obviously not one of Killian's virtues.

Killian punched the man square in the face before he could even register what he was doing. The man stumbled back before regaining balance and striking back. He pushed Killian towards a table knocking it down and following with his own punch on Killian's jaw. Killian fell backwards and landed on the floor, his head smacking the ground with a loud thud. The man moved to get on top of him and continue his assault but Killian quickly countered and pinned him to the floor throwing several punches before he felt himself being dragged away.

Unlike any other time he found himself in brawls he didn't fight back against whoever pulled him aside, he just sat on the floor, focused on his labored breathing and tried to steady his trembling hands, the familiar sharp pain from his left hand drawing his attention away from everything else.

He only looked up when he saw Ruby kneel in front of him. He couldn't bring himself to look at her, or anyone, as she looked over his hands and head for any immediate injuries. She didn't ask him anything; he wouldn't even know what to say if she did. Will came around and gave a low whistle at the sight of what was sure to be a nasty bruise blooming on the right side of his jaw.

"The man sure packs a wallop don't he?" he teased. "The Sheriff is on the way over so best stay here and avoid any more trouble, mate."

Killian only nodded, leaning his head back against the bar. It was only fair once he thought he was starting to do well things would take a turn for the worst. It was as if he was meant to be unhappy for the rest of his life, and he couldn't for the life of him figure out how to rectify it.

"I am seriously considering getting a deputy to just watch this place."

 _Bloody hell._

"That's the third fight this week, Scarlet. And it's only Wednesday."

Killian's head snapped up when he heard her voice. _Sheriff. Of bloody fucking course._ Just when he thought it couldn't get worse, Emma Swan had to show up and be the sheriff of this damned town. Killian let out a disgruntled sound escape when Emma's eyes landed on him in shock. Why did these things happen to him?

If Emma was shocked before about seeing him at the bar she didn't show any signs of it any more. She went through the motions and asked everyone involved about what happened but he knew the drill. She'd ask everyone on what they saw just to put everything on record but he was the one to throw the first punch and most of the patrons took their fellow citizen's side on the matter so it didn't come as a surprise when she came towards him with cuffs in hand. He extended his hands for her to cuff him; she raised an eyebrow at him but didn't say anything otherwise. He had half a mind to make a joke of the situation or perhaps an innuendo but thought better of it, it would only make matters worse.

He avoided eye contact with everyone, too embarrassed by his outburst to face anyone. Emma escorted him to a yellow bug which vexed him as to why the Sheriff was driving in such a vehicle.

"I was on my way home when I got the call," she explained as they walked closer to the car.

"My apologies for interrupting your night then. Guess I got carried away," he shrugged.

"Got carried away with what?" Henry said as he got out of the car.

Killian clenched his jaw in frustration and self-loathing. There was the lad who had made a promise to help him, a stranger whom he thought was a decent human being, only to find out in that moment that it was not true.

"I'll explain later kid, just go inside. Ruby is taking you home, I have to go back to the station," Emma told Henry as she opened the door to the passenger seat so Killian could get in.

"Okay," Henry shrugged. "At least I'll know where to find you tomorrow. I wanted to talk to you."

Killian laughed despite himself, "Aye, lad, you know where to find me."

Henry smiled and waved goodbye as the bug pulled away.

* * *

The next day Killian woke up to the smell of coffee brewing and loud whispers. Momentarily disoriented he remembered where he was, in the sheriff station, behind bars. His whole head throbbed and his left hand ached, Killian made a futile promise to himself that he would not get into stupid fights like the one he was in the night before, knowing full well that pact probably won't last even a week.

He looked out towards the room and notice a few people were waiting around, though he hadn't the slightest idea for what. Ruby and Will sat across from a blonde deputy which explained the loud whispers that woke him up. He saw Emma sitting in her office, hunched over files, oblivious to everybody else in the station. His gaze lingered on her and the way her blond waves fell above her shoulder. Or the way she lightly tapped her pen on her lips as she read, fully concentrated on her work.

Killian was abruptly interrupted when a pen flew past his face and hit the wall behind him.

"Oi! Stop ogling the sheriff and get off your arse. We need to get to rehearsals before Robin gets there."

"Yeah, I can't take another lecture," Ruby added.

Killian stared at them perplexed while the deputy opened his cell door. "I don't understand. I was arrested."

"You were. And now you're free to go," the deputy replied.

"David agreed to let you go earlier so you could make the rehearsal," Ruby explained.

" _With_ the condition that you'll stay out of trouble. If you are even capable of doing so,'' David eyed him.

"Aye, I'll do my best."

Ruby and Will said their goodbyes, Killian told them that he would be right behind them in a minute and made his way to the sheriff's office. He knocked and waited for her to look at him before stepping inside.

"Dave let me out early, so I was just going to say that if your boy still wanted to speak to me I'll be by the docks this afternoon. I, uh, didn't want him to think I left without a word."

"His name is David," she replied to which he dismissed it with a wave of his hand. Emma sighed, "Sorry about that."

Killian cocked his head to the side in confusion.

"About what, love?"

"About yesterday. Not showing up. It was my fault, Henry—"

"Ah, don't worry about it, love. Things happen. No ill feelings, I assure you," he smiled.

Emma was silent for a moment before she responded, "Good. I'll let Henry know where to find you."

"Thank you."

"I haven't done anything."

"You've done more than you know, love. So, thank you," Killian replied turning around to leave.

"I haven't done anything!" she yelled behind him, causing him to throw her a wink before leaving the station.


End file.
